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Compound for use in organic electroluminescent device and organic electroluminescent device

a technology of electroluminescent devices and compounds, which is applied in the direction of discharge tube luminescnet screens, anthracene dyes, applications, etc., can solve the problems of failure to emit light at high efficiency, bcp lacks reliability as hole blocker material, and the device comprising bcp shows an extremely short operating life, so as to improve the luminous efficiency of the device, secure the driving stability of the device, and high efficiency

Active Publication Date: 2011-08-09
NIPPON STEEL CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The invention provides a compound and a method for improving the efficiency and driving stability of organic electroluminescent devices. The compound has a specific indolocarbazole skeleton and can be used in various organic electroluminescent devices. The compound can be easily synthesized and has good solubility. The invention also provides a method for synthesizing the compound. The use of the compound can lead to improved luminous efficiency and driving stability of organic electroluminescent devices.

Problems solved by technology

Thereafter, europium complexes were tried in the utilization of the triplet excited state, but they failed to emit light at high efficiency.
However, BCP lacks reliability as a hole-blocking material as it tends to crystallize easily at room temperature and a device comprising BCP shows an extremely short operating life.
On the other hand, BAlq has a Tg of approximately 100° C. and a device comprising BAlq is reported to show a relatively long operating life, but the hole-blocking ability of BAlq is not sufficient and the luminous efficiency from Ir(ppy)3 drops.
Further, the disclosed indolocarbazole compounds are recommended for use as a host-transporting material and their stability is highly regarded, but the documents do not teach the use as a phosphorescent host material.

Method used

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  • Compound for use in organic electroluminescent device and organic electroluminescent device
  • Compound for use in organic electroluminescent device and organic electroluminescent device
  • Compound for use in organic electroluminescent device and organic electroluminescent device

Examples

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Effect test

example 1

Synthesis Of Compound 9

[0068]In a 200-ml three-necked flask that had been deaerated and filled with nitrogen were placed 5.0 g (44.59 mmol) of 1,2-cyclohexanedione and 12.9 g (89.21 mmol) of phenylhydrazine hydrochloride, then 145 ml of ethanol was added, and the mixture was stirred. To the contents of the flask was added 0.45 g (4.59 mmol) of concentrated sulfuric acid in drops over 5 minutes. The mixture was then heated to 65° C. and stirred at this temperature for 4 hours. The mixture was cooled to room temperature, the violet brown crystals formed were collected by filtration, reslurried twice with 50 ml of ethanol, and dried under reduced pressure to give 12.0 g (43.59 mmol, 97.7% yield) of a violet brown powder.

[0069]Then, 12.0 g (43.59 mmol) of the violet brown powder obtained above was placed in a 300-ml three-necked flask, 140 g of acetic acid and 8.0 g of trifluoroacetic acid were added, and the mixture was stirred. The mixture was then heated to 100° C. and stirred at thi...

example 2

Synthesis of Compound 40

[0072]In a 2000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 33.3 g (297.0 mmol) of 1,2-cyclohexanedione and 86.0 g (594.7 mmol) of phenylhydrazine hydrochloride, then 1000 ml of ethanol was added, and the mixture was stirred. To the contents of the flask was added 3.0 g (30.6 mmol) of concentrated sulfuric acid in drops over 5 minutes. The mixture was then heated to 65° C. and stirred at this temperature for 4 hours. The mixture was cooled to room temperature, the violet brown crystals formed were collected by filtration, reslurried twice with 500 ml of ethanol, and dried under reduced pressure to give 80.0 g (280.5 mmol, 96.3% yield) of a violet brown powder.

[0073]Then, 72.0 g (261.5 mmol) of the violet brown powder obtained above was placed in a 1000-ml three-necked flask, 720 g of acetic acid and 72.0 g of trifluoroacetic acid were added, and the mixture was stirred. The mixture was then heated to 100° C. and stirred ...

example 3

Synthesis of Compound 27

[0078]In a 2000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 33.3 g (297.0 mmol) of 1,2-cyclohexanedione and 86.0 g (594.7 mmol) of phenylhydrazine hydrochloride, then 1000 ml of ethanol was added, and the mixture was stirred. To the contents of the flask was added 3.0 g (30.6 mmol) of concentrated sulfuric acid in drops over 5 minutes. The mixture was then heated to 65° C. and stirred at this temperature for 4 hours. The mixture was cooled to room temperature, the violet brown crystals formed were collected by filtration, reslurried twice with 500 ml of ethanol, and dried under reduced pressure to give 80.0 g (280.5 mmol, 96.3% yield) of a violet brown powder.

[0079]Then, 72.0 g (261.5 mmol) of the violet brown powder obtained above was placed in a 1000-ml three-necked flask, 720 g of acetic acid and 72.0 g of trifluoroacetic acid were added, and the mixture was stirred. The mixture was then heated to 100° C. and stirred ...

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Abstract

Disclosed are an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, fully secured of driving stability, and simple in constitution and a compound for use therein. The organic electroluminescent device comprises a light-emitting layer disposed between an anode and a cathode piled one upon another on a substrate and the light-emitting layer contains a phosphorescent dopant and a compound for use in an organic electroluminescent device having two or more indolocarbazole skeletons as a host material. An example of the compound having indolocarbazole skeletons for use in the device is expressed by the following formula.

Description

TECHNICAL FIELD[0001]This invention relates to a novel compound for use in an organic electroluminescent device and to an organic electroluminescent device (hereinafter referred to as an organic EL device) and, more particularly, to an organic EL device which emits light of high luminance by simultaneous use of a phosphorescent dopant and a host compound of specific structure.BACKGROUND TECHNOLOGY[0002]An organic EL device of the simplest structure is generally constituted of a light-emitting layer sandwiched between a pair of counter electrodes and utilizes the following light-emitting phenomenon. Upon application of voltage to the electrodes, electrons are injected from a cathode and holes are injected from an anode and they recombine in the light-emitting layer; after recombination, the energy level in the conduction band goes back to the energy level in the valence band with release of energy in the form of light.[0003]In recent years, organic thin films have been used in the de...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): H01J1/63C07D487/04C09K11/06
CPCC07D487/04C09K11/06H01L51/0061H01L51/0067H01L51/0072H01L51/0073H05B33/14C09B11/04C09B57/00C09B57/008C07D519/00Y10S428/917C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1048C09K2211/1059C09K2211/1074C09K2211/1088C09K2211/1092C09K2211/185H01L51/0078H01L51/0084H01L51/0085H01L51/0087H01L51/5016H10K85/636H10K85/311H10K85/654H10K85/341H10K85/6574H10K85/6572H10K85/346H10K85/342H10K50/11H10K2101/10C07C209/00C07C243/38C07C309/37H10K85/111
Inventor KOMORI, MASAKIYAMAMOTO, TOSHIHIROKAI, TAKAHIROHOTTA, MASANORI
Owner NIPPON STEEL CHEMICAL CO LTD
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